Hotel booking strategies

I usually stay at hotels during my travels. What's the most important criteria when booking a hotel? Depends on who you ask. For me, I look for a hotel that is in a convenient location with comfortable beds, and of course at a low price.

What's the best way to book a hotel? Depends on your criteria. I don't care which hotel I stay in, so my favorite hotel booking site is priceline. In priceline, you enter your trip dates and city. Then, you pick an area of the city you want to stay in, enter a star level, and enter a price you want to pay. You enter your payment info and submit. If priceline finds a hotel that meets your criteria at your price, you got it and your card is charged. If not, you can try again but you need to change something about your criteria (dates, star level, add area). Check out this tutorial on how priceline hotel booking works. The catch about priceline: once booked, reservations cannot be changed or refunded so make sure your plans are final before bidding. And you don't get to pick your hotel - priceline assigns you a hotel based on your inputs. But the nice thing is being able to get a luxury hotel at a budget hotel price. By using priceline, I have stayed at some very nice hotels for a steal. I like to think of it this way: I pay a dirt cheap price and by booking on priceline, I'll get upgraded to a much nicer hotel at no additional cost. When I told my friend I stayed at the Westin hotel in Pasadena for $78 a night, he said "you can't even get a crappy hotel at that price". The regular rates for that Westin can easily be over $200.

Some priceline bidding tips:
1) I find downtown to be the best spot for hotels - I get a feel for how the city is laid out and it's a great starting point for exploring. This is especially true for relatively compact cities like Boston, New York, DC, Chicago, and San Francisco. Plus, downtown has easy access to public transportation so I can avoid renting a car.
2) Check out betterbidding.com, a forum where users share their priceline bookings. It also includes bidding tips, including the all important rebidding strategy.
3) Check hotel prices on hotwire, then make your first bid 80% of the lowest rate found on hotwire for the zone you want to stay in. Priceline usually beats hotwire in price.
4) Stick to 3 star level and higher. Priceline discounts at these levels are the greatest (percentage wise) and you're assured of a good quality hotel. You get the most bang for the buck. Bidding below 3 stars is risky because quality at those levels vary greatly and you could get stuck in a dump.
5) Perhaps it's because of the recession, but I've noticed that 4 star hotels are being won on priceline for almost the same price as 3 star hotels.
6) Deals are relative to the regular rates. For my recent Boston trip (see post below) I had to bid up to $130 to get a hotel in downtown Boston (I stayed with downtown because I didn't want to risk being far from a subway station). Although that is much more than I usually pay on priceline, it's a 68% discount - the lowest published rate is $404.